On The Road: How To Produce Great Work While Traveling The World

“I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.” That’s Jack Kerouac in On The Road, written in 1951 – decades before the Internet and mobile computing made it possible for us to live and work from just about anywhere.

Yet, 60 years on, with more flexibility than ever, the inertia of the familiar keeps many of us from buying that plane ticket, negotiating with our boss, and structuring a life rich with adventure and mobility. So what’s the secret to taking the plunge?To find out, I coordinated a series of interviews with a few experts who regularly pull off this sort of thing: Rolf Potts, acclaimed travel writer and author of Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel, Chris Guillebeau, a successful blogger and author (The Art of Non-Conformity) who has visited 177 countries, and London native Alex MacCaw, who spent a year traveling and writing before joining Twitter as a programmer.

What prompted you to take the plunge?

Alex: Well, I had spent some time in San Francisco working on a startup and was a bit burnt out. So, I decided to take a year off to travel, get a book published, and ultimately ended up moving to the States. It was either that or go to university or get job. And I’ve always been very bad at doing things I don’t like.

So, I pitched the idea of writing a JavaScript Web Applications book for O’Reilly and submitted an outline and they went for it. There was no advance but I had this naive belief that if I got published, it would increase my chances of working in the US and moving to San Francisco. So, I bought an around-the-world plane ticket and went for it. It was an amazing year, and one of the best decisions I’ve ever made. I can’t understand people who wait for their retirement to travel. I’d much rather optimize for experience than short-term wealth, and take the plunge.

Alex MacCaw’s round-the-world itinerary.
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Have you found it tough to stay focused and regimented? Any tips on managing yourself vs creative output vs travel schedule?

Rolf: For me it’s always been a challenge to stay focused and regimented. But if you can’t, it’s impossible to be creative and productive when you travel. My best strategy is to maintain a daily discipline, where I am writing every single day — even if it’s just one sentence. Often I’ll find that that first sentence is the most difficult task, and once you’ve created a sentence, it’s easier to create a paragraph, a page, a chapter of writing. Without that discipline and compulsion to create at least one sentence a day, I wouldn’t be nearly as productive as I have been.

I can’t understand people who wait for their retirement to travel. I’d much rather optimize for experience than short-term wealth.

Chris: Yes, it’s tough. That’s why you have to make it a habit like anything else. One thing that helps is to continually focus on deliverables, not time schedules. On any particular day I may be anywhere (right now I’m writing these answers from the island nation of Nauru, the world’s smallest republic). Therefore, the actual schedule may vary quite a bit from day to day or week to week.

However, every day I try to keep working away on things regardless of location: another 1,000 words for my next manuscript, another outline for a new business website, a column or freelance piece, and so on. At the end of the day, I know I’ll be dissatisfied with myself if I haven’t made sufficient progress.

I also give myself rewards that are tied to accomplishment. I love to read the New Yorker, New York Times, Economist, and other publications, so when there’s an article I’m especially interested in, I’ll make myself save it until I’ve accomplished something more productive.

If you’re traveling solo how do you get feedback when you’re stuck – any tips or methods for this?

Chris: When I get stuck, I think it’s more a question of motivation than anything else. The best way to recover, in my experience, is to ask myself what’s going on and find the root of the problem. Am I just jetlagged or otherwise tired? Am I ready to be done with this project? What do I feel like working on?

Don’t get me wrong, you may not always be able to work exclusively on things you feel motivated by. Completing big projects, like writing a book, require a constant tradeoff of short-term enjoyment for long-term fulfillment. Nevertheless, I try to spend much of my creative time on projects or tasks that I am genuinely excited about. This usually gives me more energy to keep moving along to the next project or task.

Photo: Chris Guillebeau, Dubai.
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Alex: I think traveling by yourself is great. It forces you to talk to people, get advice and make friends. I applied the same principals to my last book, basically half of it was crowdsourced. I put the book up on a GitHub repository and people submit pull requests the whole time. I think it’s a good idea. You have someone driving the project but getting a lot of input really helps even when you’re by yourself. Using tools like Google Talk and chatting with friends helps. Sometimes I would put together a Google doc with an idea, and send it off to various friends for feedback.Where do you create on the road?

Rolf: I’ve done some of my best work in tiny, dumpy hotel rooms. The important part isn’t the comfort so much as the isolation and the ability to focus entirely on the task at hand. Sometimes dumpy hotels are better than nice ones, since I work faster and more efficiently when my goal is to get outside and experience something nicer by the end of the day.

I’ve done some of my best work in tiny, dumpy hotel rooms.

Is there a country or region you felt more creative or inspired in?

Rolf: I don’t know that the country affects creativity so much as the person does. If you can maintain discipline in the Australian Outback, for instance, you can maintain that same discipline if you travel to Bangkok or Paris or 50 miles from your hometown. I’ve done a lot of writing in Thailand — it’s where I wrote my first book, “Vagabonding” — but I feel like the work I did there wasn’t exclusive or unique to that place. I’ve worked well in Paris, and in hotels in Peru and Egypt, and in my house on the Kansas prairie. Location is less important than self-discipline.

Alex: Cambodia was incredible, a country filled with amazing temples, scenery and food. I wrote a portion of the book on a little desert island just off Cambodia called koh rong samloem. We only had electricity for 2 hours of the day (powered by solar panels), so I had to turn my screen brightness right down and try to make the laptop’s battery last as long as possible.

Photo: Alex MacCaw, Cambodia.
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How do you fight feeling out of sorts while being constantly on the move?

Chris: I tend to go back to a lot of the same places while en route to new places. For example, I visit Hong Kong at least 3-4 times a year. Each time it’s only a short stay, but I know it well. Whenever I arrive in HKG and head to the city, I follow a routine of revisiting a few favorite areas and trying to visit at least one new area every time I go. The mashup of foreign and familiar helps with inspiration. My theory is that a certain amount of change is good, but not so much that your whole rhythm is thrown.

Any advice for someone nervous to do something like this?

Alex: I would start by rationalizing your fears and put them into context. Then work out what you’ll regret more in the future when looking back — not taking that incredible adventure while you could, or living the rat race you were stuck in? Often fears seem trivial with that perspective.

How did all this risk of travel and creation work out?

Alex: For me, it turned out really well. The book’s been published, I’ve moved to San Francisco and have my dream job at Twitter. I’ve accomplished all I initially set out to do and more. However, to be honest I never really saw this as much of a risk. The worst case scenario was that my bid for the US failed, that I would be back doing consultancy in London and my savings depleted. In the large scheme of things, that’s not a big deal at all. In the end, I believe you make your own luck to a large extent. It’s just a matter of reaching out, and taking that initial leap of faith.